Reaction #689163

Reaction equation

THF

3-methoxy-4-(2-propynyloxy)benzoyl chloride

cyclopentylmethylamine

triethylamine

→

N-cyclopentylmethyl-4-(2-propynyloxy)-3-methoxybenzamide

Yield 80.8%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   OtherThe mixture obtained
2. 2
   Filtrationwas filtered through Celite
3. 3
   ConcentrationThe filtrate was concentrated under reduced pressure

Procedure

To a mixture of 10 ml of THF and 0.3 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride were added dropwise 0.15 g of cyclopentylmethylamine and 0.16 g of triethylamine in order under ice cooling. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and it was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.31 g of N-cyclopentylmethyl-4-(2-propynyloxy)-3-methoxybenzamide (hereinafter, described as the compound 11 of the present invention) represented by the formula:

Source